Asymmetric organocatalysis of 4+3 cycloaddition reactions

被引：160

作者：

Harmata, M ^{[1
]}

Ghosh, SK ^{[1
]}

Hong, XC ^{[1
]}

Wacharasindhu, S ^{[1
]}

Kirchhoefer, P ^{[1
]}

机构：

[1] Univ Missouri, Dept Chem, Columbia, MO 65211 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 08期

关键词：

D O I：

10.1021/ja029058z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of several 4-trialkylsilyloxypentadienals with a chiral secondary amine, trifluoroacetic acid, and a diene resulted in the formation of 4 + 3 cycloaddition products, which were enantiomerically enriched. This represents the first examples of the asymmetric organocatalysis of the 4 + 3 cycloaddition reaction. 2,5-Dimethylfuran reacted with 4-trimethylsilyloxy-2,4-pentadienal in the presence of catalytic amounts of chiral amine and acid to afford a cycloadduct in 64% yield as a single diastereomer with an enantiomeric excess of 89%. Copyright © 2003 American Chemical Society.

引用

页码：2058 / 2059

页数：2

共 22 条

[1]

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